Dimethylformamide → 4-methacryloyloxybutyl (E)-3-(4-ethoxycarbonyloxyphenyl)acrylate

HRID 1735921Notes

Reaction equation

HRID 1735921 reaction equation
[CH2:1]([O:3][C:4]([O:6][C:7]1[CH:17]=[CH:16][C:10](/[CH:11]=[CH:12]/[C:13]([OH:15])=[O:14])=[CH:9][CH:8]=1)=[O:5])[CH3:2].CN(C)[CH:20]=[O:21]>S(Cl)(Cl)=O>[CH2:1]([O:3][C:4]([O:6][C:7]1[CH:17]=[CH:16][C:10](/[CH:11]=[CH:12]/[C:13]([O:15][CH2:10][CH2:9][CH2:8][CH2:7][O:6][C:20](=[O:21])[C:12]([CH3:13])=[CH2:11])=[O:14])=[CH:9][CH:8]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 12876666(2E)-3-{4-[(ethoxycarbonyl)oxy]phenyl}prop-2-enoic acid

Product 1

HCID 220777024-methacryloyloxybutyl (E)-3-(4-ethoxycarbonyloxyphenyl)acrylate

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5.2 g of 4-(E)-ethyloxycarbonyloxycinnamic acid in 20 ml of thionyl chloride and 0.05 ml of N,N-dimethylformamide was heated under reflux for 3 hours. Subsequently, excess thionyl chloride was distilled off. 3.3 g of 4-hydroxybutyl methacrylate were added dropwise to a solution of the resulting 4-(E)-ethyloxycarbonyloxycinnamoyl chloride in 15 ml of pyridine while stirring at 0° C. within 15 minutes. The reaction mixture was stirred at room temperature for a further 12 hours, then poured into water and extracted three times with 50 ml of ethyl acetate each time. The combined organic phases were dried over magnesium sulphate, filtered and subsequently concentrated. Chromatographic purification on silica gel with hexane/ethyl acetate (vol. 7:3) gave 3 g of 4-methacryloyloxybutyl (E)-3-(4-ethoxycarbonyloxyphenyl)acrylate, m.p. 54°-56° C.

Workup

  1. temperatureunder reflux for 3 hours
  2. distillationSubsequently, excess thionyl chloride was distilled off
  3. addition3.3 g of 4-hydroxybutyl methacrylate were added dropwise to a solution of the resulting 4-(E)-ethyloxycarbonyloxycinnamoyl chloride in 15 ml of pyridine
  4. stirringThe reaction mixture was stirred at room temperature for a further 12 hours
  5. additionpoured into water
  6. extractionextracted three times with 50 ml of ethyl acetate each time
  7. dry with materialThe combined organic phases were dried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationsubsequently concentrated
  10. customChromatographic purification on silica gel with hexane/ethyl acetate (vol. 7:3)

Sources & evidence

ORD record
ord-47d4ecd3d19849c194826fdd0827041e
Source dataset
uspto-grants-1996_07
Patent number
US05539074

Reaction notes

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